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Beilstein J. Org. Chem. 2015, 11, 504–513, doi:10.3762/bjoc.11.57
Graphical Abstract
Scheme 1: The key experimental results on the DDC 1 reactions with thioketones 2 [19-21].
Figure 1: Diazo compounds 1 and thioketones 2 used in the study.
Scheme 2: General scheme for reactions of DDC 1 with thiobenzophenone (2a).
Figure 2: Optimized structures of the lowest energy Z,E-conformers of diazo compounds 1a–d.
Scheme 3: Reactions of the intermediate thiocarbonyl ylide 7'd via competative 1,5-EC (a) or 1,3-EC (b) follo...
Beilstein J. Org. Chem. 2013, 9, 2751–2761, doi:10.3762/bjoc.9.309
Figure 1: Thioketones 1 and diazodicarbonyl compounds 2.
Figure 2: ORTEP plot [17] of the molecular structure of the 1,3-oxathiole 3a (50% probability ellipsoids; arbitra...
Scheme 1: Reaction of diazocarbonyl compounds 2a,c,e with adamantane-2-thione (1b).
Scheme 2: Three possible pathways A, B and C for the formation of 1,3-oxathioles 3,7 and thiiranes 5 and 8 fr...
Scheme 3: Two competitive transformations of dibenzoyldiazomethane (2b) at 80 °С leading to 3b and 4b.
Scheme 4: Interconversion of 1,3-oxathiole 3e and C=S ylide 6e’ accompanied by 1,3-electrocyclization and des...
Figure 3: Energy profile for the transformation of 1,3-oxathiole 3e to alkene 5e. Relative free energies (kca...